Aliphatic–aromatic stacking interactions in cyclohexane–benzene are stronger than aromatic–aromatic interaction in the benzene dimer

Abstract

Stacking interactions between cyclohexane and benzene were studied in crystal structures from the Cambridge Structural Database and by ab initio calculations. Calculated at the very accurate CCSD(T)/CBS level of theory, the cyclohexane–benzene interaction energy is −3.27 kcal mol⁻¹, which is significantly stronger than the interaction in the benzene dimer (−2.84 kcal mol⁻¹) indicating the importance of aliphatic–aromatic interactions.